NO146983B - APPLICATION OF ALFA-ACYLOXY-N, N - Google Patents
APPLICATION OF ALFA-ACYLOXY-N, N Download PDFInfo
- Publication number
- NO146983B NO146983B NO773006A NO773006A NO146983B NO 146983 B NO146983 B NO 146983B NO 773006 A NO773006 A NO 773006A NO 773006 A NO773006 A NO 773006A NO 146983 B NO146983 B NO 146983B
- Authority
- NO
- Norway
- Prior art keywords
- carbon atoms
- activators
- acyloxy
- compounds
- radicals
- Prior art date
Links
- 239000012190 activator Substances 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001033 ether group Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical group ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000004061 bleaching Methods 0.000 description 8
- 230000000694 effects Effects 0.000 description 6
- 238000005406 washing Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- -1 perborates Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VXVZLUGHWLVUEA-UHFFFAOYSA-N (1,3-diacetamido-2-methyl-1,3-dioxopropan-2-yl) acetate Chemical compound CC(=O)NC(=O)C(C)(OC(C)=O)C(=O)NC(C)=O VXVZLUGHWLVUEA-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 239000007844 bleaching agent Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000004453 electron probe microanalysis Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- UFZOPKFMKMAWLU-UHFFFAOYSA-N ethoxy(methyl)phosphinic acid Chemical compound CCOP(C)(O)=O UFZOPKFMKMAWLU-UHFFFAOYSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000001469 hydantoins Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 239000012418 sodium perborate tetrahydrate Substances 0.000 description 1
- IBDSNZLUHYKHQP-UHFFFAOYSA-N sodium;3-oxidodioxaborirane;tetrahydrate Chemical compound O.O.O.O.[Na+].[O-]B1OO1 IBDSNZLUHYKHQP-UHFFFAOYSA-N 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/42—Amides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/08—Preparations for bleaching the hair
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/39—Organic or inorganic per-compounds
- C11D3/3902—Organic or inorganic per-compounds combined with specific additives
- C11D3/3905—Bleach activators or bleach catalysts
- C11D3/3907—Organic compounds
- C11D3/3917—Nitrogen-containing compounds
Description
Foreliggende oppfinnelse angår anvendelse av a-acyl-oksy-N,N'-polyacylmalonamider som aktivatorer for uorganiske og organiske perforbindelser, spesielt for hydrogenperoksyd, addisjonsprodukter derav med organiske stoffer slik som urea og dicykloheksylamin, samt disses uorganiske persalter slik som perborater, perkarbonater og perfosfater. The present invention relates to the use of α-acyl-oxy-N,N'-polyacylmalonamides as activators for inorganic and organic per compounds, especially for hydrogen peroxide, addition products thereof with organic substances such as urea and dicyclohexylamine, as well as their inorganic per salts such as perborates, percarbonates and perphosphates.
Virkningen av vandige oppløsninger av perforbindél—-ser som oksydasjonsmidler og blekemidler blir ikke effektiv før ved temperaturer over 70°C og fortrinnsvis mellom 80 og 100°C. The effect of aqueous solutions of perforbindels as oxidizing agents and bleaching agents does not become effective until temperatures above 70°C and preferably between 80 and 100°C.
Den kjente teknikk beskriver tallrike produkter som oppviser egenskaper som aktivatorer for perforbindelser, dvs. som tillater å oppnå en oksyderende virkning eller en blekevirkning hurtigere enn det man vanligvis ser, eller videre å utvikle denne virkning under temperaturbetingelser langt under det som er nødvendig i tilfelle deres fravær, og alle disse forbindelser er karakterisert ved at de har én eller flere per-hydrolyserbare funksjoner. The prior art describes numerous products which exhibit properties as activators for per compounds, i.e. which allow to obtain an oxidizing effect or a bleaching effect faster than is usually seen, or further to develop this effect under temperature conditions far below what is necessary in the case of their absence, and all these compounds are characterized by having one or more per-hydrolysable functions.
På området bleking er det kjent en rekke aktivator-forbindelser med kommersiell anvendelse. Litteraturen på dette område nevner spesielt poly-N-acetylerte heterocykler av typen hydantoiner, benzimidazoler og diketopiperaziner. Imidlertid har denne utvikling ikke fortsatt fordi stoffene oppviser alvorlige mangler idet de er ustabile overfor fuk-tighet og således hydrolyserer spontant, hvorved de hurtig minster sin aktivatoregenskap. Videre nødvendiggjør disse produkter spesielle forholdsregler med henblikk på lagring, behandling eller tilsetning til andre bestanddeler slik de f.eks. inngår i den vanlige sammensetning i et vaskepulver. Forskjellige løsninger er foreslått for å oppheve disse mangler: Innkapsling, separat kondisjonering, tilsetning av tørke-midler, men ingen av disse har vært tilfredsstillende, enten fordi de har gitt praktiske tekniske problemer eller fordi de har ført til en betydelig økning av prisen. In the area of bleaching, a number of activator compounds with commercial use are known. The literature in this area mentions in particular poly-N-acetylated heterocycles of the type hydantoins, benzimidazoles and diketopiperazines. However, this development has not continued because the substances show serious shortcomings in that they are unstable to moisture and thus hydrolyze spontaneously, whereby they quickly lose their activator properties. Furthermore, these products necessitate special precautions with a view to storage, treatment or addition to other components as they e.g. included in the usual composition of a washing powder. Various solutions have been proposed to overcome these shortcomings: encapsulation, separate conditioning, addition of drying agents, but none of these have been satisfactory, either because they have caused practical technical problems or because they have led to a significant increase in price.
Det foreligger således et industrielt behov for aktivatorer for perforbindelser, aktivatorer som er stabile under de vanlige betingelser for lagring og behandling. There is thus an industrial need for activators for per compounds, activators which are stable under the usual conditions for storage and processing.
Foreliggende oppfinnelse har til hensikt å løse de ovenfor angitte problemer og angår anvendelse av a-acyloksy-N,N<1->polyacylmalonamider med formelen: The present invention aims to solve the above-mentioned problems and concerns the use of α-acyloxy-N,N<1->polyacylmalonamides with the formula:
der R^, I^, R3, R 4/ R5 og Rg som er like eller forskjellige betyr hydrogen, lineære alkylrester med 1-11 karbonatomer, forgrenede alkyl- og cykloalkylrester med 3-12 karbonatomer, hydrokarbonrester med 6-12 karbonatomer, som omfatter minst én aromatisk kjerne, eller der R , R£, R-j og R^ er definert som ovenfor mens R,, og/eller R^ er en acylgruppe COR^, der R^ er hydrogen eller en lineær eller forgrenet alkylrest med 1-12 karbonatomer eller en hydrokarbonrest med 6-12 karbonatomer omfattende minst én aromatisk kjerne, hvilke rester eventuelt kan være substituert med én eller flere hydroksy-, klor-, brom-, fluor-, jod-, nitro-, alkoksy-, amino-, ester-, amid- og etergrupper, som aktivatorer for perforbindelser, særlig for hydrogenperoksyd og addisjonsforbindelser derav. where R^, I^, R3, R4/R5 and Rg which are the same or different mean hydrogen, linear alkyl radicals with 1-11 carbon atoms, branched alkyl and cycloalkyl radicals with 3-12 carbon atoms, hydrocarbon radicals with 6-12 carbon atoms, which comprises at least one aromatic nucleus, or where R, R£, R-j and R^ are defined as above while R,, and/or R^ is an acyl group COR^, where R^ is hydrogen or a linear or branched alkyl residue with 1- 12 carbon atoms or a hydrocarbon residue with 6-12 carbon atoms comprising at least one aromatic core, which residues may optionally be substituted with one or more hydroxy, chlorine, bromine, fluorine, iodine, nitro, alkoxy, amino, ester, amide and ether groups, as activators for per compounds, especially for hydrogen peroxide and addition compounds thereof.
Som illustrasjon kan a-acyloksy-N,N'-polyacylmalon-amidene av formel (I) være a-acetoksy-a-metyl-N,N'-di-acetylmalonamid, a-propionoksy-a-metyl-N,N'-dipropionylmalonamid og a-acetoksy-ot-mety 1-N, N '-dipropionylmalonamid. By way of illustration, the α-acyloxy-N,N'-polyacylmalonamides of formula (I) may be α-acetoxy-α-methyl-N,N'-di-acetylmalonamide, α-propionoxy-α-methyl-N,N' -dipropionylmalonamide and α-acetoxy-ot-methyl 1-N,N'-dipropionylmalonamide.
En spesielt fordelaktig måte for anvendelse av aktivatorene ifølge oppfinnelsen består i å tilsette disse til perforbindelsen i en mengde på ca. 0,33 mol pr. mol perforbindelse som skal aktiveres. Imidlertid kan man etter behov arbeide med et underskudd eller overskudd av aktivator og med molforhold mellom aktivator og perforbindelse som ligger mellom 0,1 og 10. A particularly advantageous way of using the activators according to the invention consists in adding these to the per compound in an amount of approx. 0.33 mol per mol per compound to be activated. However, if necessary, one can work with a deficit or excess of activator and with a molar ratio between activator and per-compound that is between 0.1 and 10.
Aktivatorene av formel (I) kan benyttes i The activators of formula (I) can be used in
alle tilfeller der en perforbindelse benyttes for å oppnå en oksyderende eller blekende virkning, f.eks. ved bleking av tekstilfibre, olje, fett og voks, behandling av hår eller hud på kosmetologisk måte, passivering av metalloverflater, rense-teknikker, desinfeksjon og sterilisering. all cases where a compound is used to achieve an oxidizing or bleaching effect, e.g. by bleaching textile fibres, oil, fat and wax, treating hair or skin in a cosmetological way, passivating metal surfaces, cleaning techniques, disinfection and sterilisation.
Aktivatorene av formel (I) som tilsettes til perforbindelser eller en sammensetning inneholdende én eller flere perforbindelser, f.eks. et vaskemiddel, tilsikter å oppnå en blekende eller oksyderende virkning adskillig hurtigere ved en gitt temperatur, de tillater likeledes på samme måte å oppnå den samme blekevirkning ved å arbeide ved lavere temperatur . The activators of formula (I) which are added to per compounds or a composition containing one or more per compounds, e.g. a detergent, aims to achieve a bleaching or oxidizing effect much faster at a given temperature, they likewise allow the same bleaching effect to be achieved by working at a lower temperature.
Ved nærvær av natriumperborat i et vaskemiljø tillater f.eks. aktivatorene ifølge oppfinnelsen ved temperaturer mellom 30 og 50°C å oppnå en blekevirkning som i det vesent-lige er ekvivalent den som oppnås ved aktivatorenes fravær ved høyere temperaturer i størrelsesorden 80°C. In the presence of sodium perborate in a washing environment allows e.g. the activators according to the invention at temperatures between 30 and 50°C to achieve a bleaching effect which is essentially equivalent to that achieved in the absence of the activators at higher temperatures of the order of 80°C.
De følgende eksempler skal illustrere oppfinnelsen. The following examples shall illustrate the invention.
Eksempel 1- 3 Example 1-3
I et rom i et "AHIBA" bad med en temperatur på 40°C ble det tilført 250 ml av en vandig o<p>pløsning inneholdende 5 g/l av et vaskemiddel med følgende sammensetning: In a room in an "AHIBA" bath with a temperature of 40°C, 250 ml of an aqueous solution containing 5 g/l of a detergent with the following composition was added:
samt 1,7 g/l natriumperborattetrahydrat. as well as 1.7 g/l sodium perborate tetrahydrate.
I et annet rom ble den samme oppløsning tilsatt, men aktivatoren som skulle prøves i en konsentrasjon på In another room, the same solution was added, but the activator to be tested at a concentration of
1 g/l. 1 g/l.
I hvert av rommene ble det anbragt et stykke bomullsvevnad "EMPA", impregnert med standardiserte vinflek-ker . In each of the rooms, a piece of cotton fabric "EMPA" was placed, impregnated with standardized wine stains.
Etter 15 minutters vasking ble vevnadene skylt under en strøm av kaldt vann og deretter tørket ved omgivelsestem-peraturer. Blekekraften defineres som forskjellen mellom hvithetsindeksen (målt ved hjelp av et "ELREPHO" spektrofoto-meter med filter nr. 6) før og etter vasking, angitt som prosent av et hvithetsmaksimum på 100. After 15 minutes of washing, the tissues were rinsed under a stream of cold water and then dried at ambient temperatures. The bleaching power is defined as the difference between the whiteness index (measured using an "ELREPHO" spectrophotometer with filter No. 6) before and after washing, expressed as a percentage of a whiteness maximum of 100.
Man oppnår følgende resultater: The following results are achieved:
Eksempel 4- 6 Example 4-6
Man arbeider under de samme betingelser som ovenfor, men med en vasketemperatur på 20°C i stedet for 4 0°C. You work under the same conditions as above, but with a washing temperature of 20°C instead of 40°C.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR7626325A FR2363629A1 (en) | 1976-09-01 | 1976-09-01 | ACTIVATORS FOR PERCOMPOSES |
Publications (3)
Publication Number | Publication Date |
---|---|
NO773006L NO773006L (en) | 1978-03-02 |
NO146983B true NO146983B (en) | 1982-10-04 |
NO146983C NO146983C (en) | 1983-01-26 |
Family
ID=9177298
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO773006A NO146983C (en) | 1976-09-01 | 1977-08-31 | APPLICATION OF ALFA-ACYLOXY-N, N |
Country Status (16)
Country | Link |
---|---|
JP (1) | JPS6031879B2 (en) |
BE (1) | BE858048A (en) |
BR (1) | BR7705823A (en) |
CA (1) | CA1088954A (en) |
CH (1) | CH626398A5 (en) |
DE (1) | DE2738976C3 (en) |
DK (1) | DK145829C (en) |
ES (1) | ES462018A1 (en) |
FR (1) | FR2363629A1 (en) |
GB (1) | GB1563635A (en) |
IE (1) | IE45372B1 (en) |
IT (1) | IT1083604B (en) |
LU (1) | LU78047A1 (en) |
NL (1) | NL7709591A (en) |
NO (1) | NO146983C (en) |
SE (1) | SE434960B (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2831899A1 (en) * | 1978-07-20 | 1980-02-07 | Basf Ag | USE OF ACYLATED PHOSPHORIC OR SULFURIC ACID AS A CLEAR BLEACH ACTIVATOR FOR DETERGENT-RELEASING COMPONENTS CONTAINING ACTIVE OXYGEN |
US4199466A (en) * | 1978-08-21 | 1980-04-22 | Shell Oil Company | Activated bleaching process and compositions therefor |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR204021A1 (en) * | 1973-12-04 | 1975-11-12 | Hoechst Ag | WASHING AND WHITENING OXIDIZING AGENTS CONTAINING INORGANIC PERCOMPOSES AND TEXTILE WHITENING PROCEDURE |
JPS5313355B2 (en) * | 1974-03-18 | 1978-05-09 | ||
FR2363541A1 (en) * | 1976-09-01 | 1978-03-31 | Ugine Kuhlmann | ACYLOXY-N, N 'DIACYLMALONAMIDES AND THEIR METHOD OF PREPARATION |
-
1976
- 1976-09-01 FR FR7626325A patent/FR2363629A1/en active Granted
-
1977
- 1977-08-24 GB GB35517/77A patent/GB1563635A/en not_active Expired
- 1977-08-24 BE BE1008343A patent/BE858048A/en not_active IP Right Cessation
- 1977-08-25 IE IE1772/77A patent/IE45372B1/en not_active IP Right Cessation
- 1977-08-25 JP JP52101184A patent/JPS6031879B2/en not_active Expired
- 1977-08-26 IT IT68921/77A patent/IT1083604B/en active
- 1977-08-29 SE SE7709694A patent/SE434960B/en not_active IP Right Cessation
- 1977-08-30 LU LU78047A patent/LU78047A1/en unknown
- 1977-08-30 DE DE2738976A patent/DE2738976C3/en not_active Expired
- 1977-08-30 DK DK383677A patent/DK145829C/en not_active IP Right Cessation
- 1977-08-31 NL NL7709591A patent/NL7709591A/en not_active Application Discontinuation
- 1977-08-31 CA CA285,882A patent/CA1088954A/en not_active Expired
- 1977-08-31 ES ES462018A patent/ES462018A1/en not_active Expired
- 1977-08-31 BR BR7705823A patent/BR7705823A/en unknown
- 1977-08-31 NO NO773006A patent/NO146983C/en unknown
- 1977-09-01 CH CH1070277A patent/CH626398A5/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
FR2363629A1 (en) | 1978-03-31 |
DK145829C (en) | 1983-09-05 |
NL7709591A (en) | 1978-03-03 |
DE2738976A1 (en) | 1978-03-02 |
IE45372B1 (en) | 1982-08-11 |
DK383677A (en) | 1978-03-02 |
IT1083604B (en) | 1985-05-21 |
FR2363629B1 (en) | 1980-05-30 |
BE858048A (en) | 1978-02-24 |
DK145829B (en) | 1983-03-14 |
JPS5330485A (en) | 1978-03-22 |
NO773006L (en) | 1978-03-02 |
SE434960B (en) | 1984-08-27 |
JPS6031879B2 (en) | 1985-07-24 |
BR7705823A (en) | 1978-06-27 |
GB1563635A (en) | 1980-03-26 |
LU78047A1 (en) | 1979-05-23 |
DE2738976C3 (en) | 1980-02-07 |
ES462018A1 (en) | 1978-12-16 |
SE7709694L (en) | 1978-03-02 |
CA1088954A (en) | 1980-11-04 |
DE2738976B2 (en) | 1979-06-07 |
NO146983C (en) | 1983-01-26 |
CH626398A5 (en) | 1981-11-13 |
IE45372L (en) | 1978-03-01 |
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